N-phenylisatin mediated ketone-carboxylic acid conversion reaction method

Through the N-phenyl isatin-mediated ketone-carboxylic acid conversion reaction method, the TfOH catalyst and cyclohexane solvent are used to achieve efficient conversion of ketone organic matter to carboxylic acid and its derivatives under mild conditions, solving the problem of the need for excessive oxidants and precious metals in the prior art, and achieving a wide range of substrates and efficient carboxylic acid synthesis.

CN119684105AActive Publication Date: 2025-03-25GUIZHOU MEDICAL UNIV
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Patent Information

Application Number
CN202411873663.4
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2024-12-18
Publication Date
2025-03-25
Estimated Expiration
2044-12-18

AI Technical Summary

Technical Problem

The prior art requires excessive oxidizing agents, high temperatures and precious metal catalysis in the preparation of carboxylic acids and their derivatives, limiting the range of substrates and the efficiency of synthesis.

Method used

The keto-carboxylic acid conversion reaction method mediated by N-phenyl isatin, and TfOH is used as a catalyst and cyclohexane as a solvent to achieve efficient conversion of keto organic matter to carboxylic acid and its derivatives under mild conditions.

Benefits of technology

This method does not require excessive oxidants and precious metals, has a wide range of substrates, high atomic utilization rate, simple post-treatment, green and pollution-free, and can efficiently construct carboxylic acid groups and active complex functional molecules containing indigo skeletons under mild reaction conditions.

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Abstract

The invention provides an N-phenyl isatin-mediated ketone-carboxylic acid conversion reaction method, which comprises the following steps: mixing an isatin skeleton-containing compound and a ketone organic matter, adding a catalyst and a solvent into the mixture, reacting for 12-24 hours at the temperature of 80-100 DEG C, carrying out quenching reaction, drying an organic layer, carrying out rotary evaporation to remove the solvent, and carrying out chromatographic purification on residues, thereby obtaining the N-phenyl isatin-mediated ketone-carboxylic acid. A carboxylic acid group and an active complex functional molecule containing an isatin skeleton are simultaneously constructed through a one-step reaction; the method overcomes the defects that excessive oxidant, high temperature, precious metal catalysis and the like are needed in the prior art, raw materials are simple and easy to obtain, reaction conditions are mild and safe, and reaction products have huge potential application value in the field of medicine.
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